How to create an action for x amount of times a task is performed

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You can use loop activities to processes your tasks. Inside your loop, put some validation before start the next one. For example, check if login time out occurs, if so, you call other workflow just for login. Then your process continues without break.

If you need more robust solution with retry mechanism, processes task individually and so on the better choice is ReFramework

If you perform simple task, you can create additional step for check login. Specially create a workflow only for login purpose that you can call in timeout case or even put user interaction activity like click to make some interaction with this windows to prevent timeout. But some time to process 1 task the time necessary is more than timeout ones. So the additional step is a good practices.

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